There are certain adhesive applications for which solvent resistance is highly desirable. These include automotive, aerospace, industrial and consumer labels where exposure to aromatic aliphatic solvents and oils occurs. Solvent resistant adhesives are also required for labels used by analytical laboratories such as environmental or medical labs to prevent loss of critical sample identification information. Further applications include electronic labels or masked areas undergoing further processes; dry cleaning labels for garments; degreasing operations where identification labels or masked off areas are required. Adhesive properties of many pressure sensitive or heat activated adhesives are well suited for use with labels on various substrates, however these are not solvent resistant and therefore it is highly desirable that a solvent-resistant adhesive be provided.
US20040122176A1 Chao, H. discloses compositions of non-branched and branched polybutadienes with terminal hydroxyl functionality reacted with polyisocyanates that are chain extended with difunctional chain extender. No mention is made for chain termination with a monofunctional composition such as an alcohol, monoisocyanate or the crosslinking via peroxides or silicone hydrosilylation.
U.S. Pat. No. 5,223,575 Mori, M. discloses moisture crosslinkable primer compositions for polyolefins comprising the reaction product of a hydrogenated polybutadiene, polyisocyanate prepolymer with 0.1 to 10 wt % isocyanate content further reacted with an aminosilane. No disclosure of peroxide crosslinking is made and the hydrogenated polybutadiene compositions disclosed would not be reactive by silicone hydrosilylation for further crosslinking.
Solvent resistant adhesives are disclosed in the art. For example JP 56082863 Sadamitsu, K., et. al., teaches a thermoplastic polystyrene-polybutadiene block copolymer or a mixture thereof with another thermoplastic rubber of ethylene-vinyl acetate copolymer combined with of an acryl-modified polybutadiene.
JP 57207663 Ueno, H. discloses a compound comprised of ethylenic ionomer resin, a polyurethane resin, a polyethylene resin, a polyamide resin, a polyester resin, an agent for the thermal curing of a synthetic resin, and a thickener.
JP 59172575 Mishima, M. et. al., discloses a solvent resistant hot-melt adhesive comprised of a polyester amide polyurethane containing terminal alkoxyl groups prepared by reacting an aminoalkylalkoxysilane compound with a polyester-amide containing terminal isocyanate groups.
JP 59174672 Mishima, M. et. al., discloses a solvent resistant acrylic adhesive comprised of the reaction product of a vinyl compound (e.g., methyl acrylate, isobutyl methacrylate, etc.) and a vinyl dioxazolone compound.
JP 61047774 Okada, C. et. al., discloses a solvent resistant adhesive comprised of amino group terminated polyamide resin reacted with a isocyanate group-containing alkoxysilane that is the additional product of for example hexamethylene diisocyanate and 3-aminopropyltriethoxy-silane.
JP 61218631 Okada, C. et. al., discloses a solvent resistant adhesive comprised of a silane modified polyester resin obtained by reacting a polyester resin containing a hydroxyl group with an isocyanate group-containing hydrolyzable organosilicon compound.
JP 61218672 Mishima, M. et. al., discloses a solvent resistant acrylic adhesive comprised of an unsaturated polyester resin having terminal ethylenic groups the reaction product of a ethylenic compound having isocyanate groups with terminal hydroxyl groups or carboxyl groups of an unsaturated polyester resin.
JP 61218673 Mishima, M. et. al., further discloses a solvent resistant acrylic adhesive comprised of an unsaturated polyester resin having terminal ethylenic double bonds obtained by reacting epoxy (meth) acrylate with the terminal carboxyl groups of an unsaturated polyester resin having ethylenic double bond in the molecule.
JP 62057480 Yamazaki, H. et. al., discloses a solvent resistant adhesive comprised of a polyamide resin having terminal ethylenic double bonds obtained by reacting a compound having aziridinyl and ethylenic groups with terminal carboxyl groups of a polyamide resin.
JP 62057479 Yamazaki, H. et. al., discloses a solvent resistant adhesive comprised of an unsaturated polyester resin having both terminal and in chain ethylenic double bonds obtained by reacting a compound having aziridinyl and ethylenic groups with terminal carboxyl groups of an unsaturated polyester resin.
JP 62057478 Yamazaki, H. et. al., discloses a solvent resistant adhesive comprised of an unsaturated polyester resin having terminal and in chain ethylenic double bonds obtained by reacting a terminal hydroxyl group of an unsaturated polyester resin with an epoxy (meth)acrylate.
JP 62089782 Oguro, K. et. al., discloses a solvent resistant adhesive obtained by reaction between a high-molecular weight diol preferably a polyester diol of polyethylene-butylene-adipate, a divalent isocyanate compound, a chain extender and a hindered nitrogen atom compound such as containing a piperizine ring.
JP 61218631 Okada, C., discloses a solvent resistant adhesive comprised of a polyamide resin having terminal amino groups reacted with a (meth)acrylic monomer such as an isocyanate-modified (meth)acrylate to give a polyamide resin having (meth)acryloyl groups. A radical generator such as a peroxide is used to cure said compositions.
JP 03259981 Nishikawa, A. et. al., discloses a solvent resistant adhesive comprised of a composition prepared by compounding a block copolymer and an isocyanate pre-polymer. The block copolymer comprises a block consisting of at least two kinds of aromatic vinyl monomers and a block consisting of at least one kind of a conjugated diene monomer, and at least 50% of carbon-carbon double bonds in the block consisting of the diene monomer have been hydrogenated (e.g., a hydrogenated styrene-isoprene-styrene triblock copolymer). The isocyanate pre-polymer is obtained by reacting an isocyanate compound with a liquid polymer which comprises a polymer of isoprene or isoprene-butadiene mixture and has 1.5-5.0 hydroxyl groups in the molecule and in which at least 50% of carbon-carbon double bonds have been hydrogenated.
JP 09165565 Nishikawa, A. et. al., discloses a solvent resistant adhesive comprised of blending a base polymer with a tackifier resin and optionally a softening agent or a wax, a block copolymer which comprises one or more hydrogenated butadiene polymer blocks, one or more of aromatic vinyl compound polymer blocks and one or more polymer blocks substantially having an olefin polymer structure.
Despite the disclosure contained in the above-described art, there is still a need for new forms of solvent resistant adhesive compositions and to laminates having a backing material coated with such adhesives.